US6150550A - Process for preparing alkoxysilanes - Google Patents

Process for preparing alkoxysilanes Download PDF

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US6150550A
US6150550A US09/210,735 US21073598A US6150550A US 6150550 A US6150550 A US 6150550A US 21073598 A US21073598 A US 21073598A US 6150550 A US6150550 A US 6150550A
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Stefan Bade
Udo Robers
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Evonik Operations GmbH
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Huels AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages

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  • the present invention relates to an improved process for preparing alkoxysilanes from halosilanes and alcohols.
  • Alkoxysilanes are important industrial intermediates or end products in organosilane chemistry. They are used, inter alia, as coupling agents in composite materials, for example in the coatings and glass fiber industry, in the foundry and in the manufacture of adhesives, and for the manufacture of elastomers. Individual examples which can be mentioned are silanized glass fibers, polymer systems or silicone systems reinforced by fine materials, e.g., permanently flexible sealants, silica-filled rubber articles, e.g. tires, the modification of hydroxy-functional surfaces, the silane polycondensation to give polyorganosiloxanes and preservatives for buildings and other structures.
  • the alkoxysilanes are prepared by reacting halosilanes, which can contain one or more halogen atoms, with an alcohol, for example an alkanol or an alkoxyalkanol, in accordance with the general equation below:
  • R 1 , R 2 , R 3 , R 4 and X, a, b and c have the meaning specified below.
  • the stoichiometric amount of hydrogen halide HX is therefore always formed.
  • the halosilanes are reacted with the alcohol either batchwise or continuously, the hydrogen halide formed being converted into the gas phase or remaining bound in the liquid phase.
  • Customary techniques for removing the hydrogen halide by conversion into the gas phase are stripping, distillation (also reactive distillation). Processes of this type are described, inter alia, in DE 20 61 189 and U.S. Pat. No.
  • a sought-after alkoxysilane is (3-chloropropyl)methyldimethoxysilane (CPMDMO), which is formed from (3-chloropropyl)methyldichlorosilane and methanol.
  • CPMDMO (3-chloropropyl)methyldimethoxysilane
  • the reaction product of the first stage is favored over the dialkoxysilane. This is shown by comparing the equilibrium constants, that for the first stage at room temperature being considerably greater than 1, but that for the second stage being only 0.4.
  • the reaction is carried out batchwise in a stirred-tank reactor, and the resulting hydrogen halide is removed from the reaction mixture by distillation. The yield is about 60%.
  • solvents in the removal of hydrogen halide are likewise described.
  • the solvents serve to decrease the viscosity of the reaction mixture, which is always a single phase (DE-A 20 61 189), or to depress the boiling point of the reaction mixture, which is always a single phase (DE-A 28 00 017, DE-A 32 36 628).
  • the use of solvents in a two-phase reaction mixture has not yet been described.
  • stirred tanks e.g. GB 674 137
  • tubular reactors--(DE-A 20 33 373) stirred tanks equipped with a column (e.g. --DE-A 32 36 328) and reaction-distillation columns (e.g., U.S. Pat. No. 4,298,753).
  • R 1 is hydrogen, alkyl, alkenyl, aryl or haloalkyl
  • R 2 is hydrogen or alkyl
  • R 3 is hydrogen or alkyl
  • R 4 is alkyl or alkoxyalkyl
  • a, b and c are identical or different and can be 0, 1, 2 or 3, with the proviso that a+b+c ⁇ 3,
  • R 1 , R 2 and R 3 and a, b, and c are as defined above, and X is fluorine chlorine, bromine or iodine, with an alcohol of the general formula
  • FIG. 1 is a block diagram of a plant for carrying out the process according to the invention batchwise.
  • FIG. 2 is a block diagram of a plant in which the process according to the invention can be carried out continuously.
  • the reaction to produce the alkoxysilanes may be termed a reactive extraction, since. simultaneously with the chemical reaction of the halosilane II with the alcohol III, a reaction product, namely the hydrogen halide being formed, is extracted into one of the phases, namely the alcohol phase.
  • the process according to the invention is associated with a number of surprising advantages.
  • the reaction takes place at the interface of the two separate phases of the reaction mixture, the resulting alkoxysilane very largely remains in the nonpolar phase and thereby avoids contact with the hydrogen halide which is dissolved in the polar alcohol phase. Since the nonpolar phase is virtually free from hydrogen halide, on the one hand, the secondary reaction of the alkoxysilane to form siloxanes which are higher boiling or can no longer be distilled is virtually completely prevented and, on the other hand, the equilibrium of the alkoxylation reaction is shifted towards the alkoxysilanes or, in the case of halosilanes having more than one halogen atom, in the direction of the completely alkoxylated silanes. Furthermore, there is no conversion of haloalkyl substituents R 1 into alkoxyalkyl radicals.
  • the process proceeds at low temperatures, which contributes to suppressing the unwanted secondary reactions. Especially, higher-boiling alcohols need not be vaporized, as is the case in the reactive distillation.
  • the process according to the invention is independent of the boiling positions of the chlorosilanes II, the alcohols III and the alkoxysilanes I. As a result, the reaction can generally be carried out at atmospheric pressure.
  • a desired result of the reactive extraction according to the invention is an improved selectivity of the formation of the (completely alkoxylated) alkoxysilane and thus a higher yield, which can considerably exceed 90% when the process is carried out continuously.
  • halosilanes having more than one halogen atom are used, all halogen atoms are replaced by alkoxy groups. This facilitates the work-up of the nonpolar phase (and improves the yield), because no incompletely alkoxylated products need to be removed.
  • the polar alcohol phase can be worked up in a simple manner by distillation. If appropriate, the alkoxysilanes, which are present in the alcohol phase in accordance with the distribution equilibrium, can be extracted with fresh nonpolar solvent before the distillation and recycled to the reaction.
  • the hydrogen halide removed is highly pure. It can be used directly for many purposes and does not need to be disposed of by neutralization with salt formation.
  • R 1 is an alkyl, alkenyl or haloalkyl radical having 1 to 6 carbon atoms (and, e.g., 1 to 3, or more, halogen atoms) or an aryl radical having 6 to 10 carbon atoms;
  • R 2 and R 3 independently of one another are hydrogen or alkyl radicals having 1 to 6 carbon atoms;
  • R 4 is an alkyl radical having 1 to 6, in particular 1 or 2, carbon atoms or an alkoxyalkyl radical having 3 to 8 carbon atoms and 1 or 2 oxygen atoms; and X is chlorine or fluorine.
  • alkyl radicals which can be present in the preferred alkoxysilanes I and the preferred starting materials II and III, mention may be made of methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methyl-2-propyl, 1-pentyl and 1-hexyl.
  • Preferred alkenyl radicals are, for example, vinyl, 1- and 2-propenyl, 1-butenyl and 5-hexenyl.
  • preferred haloalkyl radicals are chloromethyl, 2-chloroethyl, 3-chloropropyl and 3,3,3-trifluoropropyl.
  • the preferred aryl radicals include phenyl, tolyl, styryl, 1-naphthyl and benzyl.
  • the preferred alkoxyalkyl radicals mention may be made of, for example, 2-methoxyethyl and 2-(2'-methoxyethyl)ethyl.
  • halosilanes II to be reacted mention may be made of, for example, trichlorosilane, methyltrichlorosilane, dimethyldichlorosilane, trimethylchlorosilane, diethyldichlorosilane, (3-chloropropyl)trichlorosilane, (3-chloropropyl)methyldichlorosilane, (3,3,3-trifluoropropyl)methyldichlorosilane, vinyltrichlorosilane, propyltrichlorosilane, isobutyltrichlorosilane and n-octyltrichlorosilane.
  • Examples of preferred suitable alcohols III are methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-hexanol and 2-methoxyethanol (or methyl glycol) and 2-ethoxyethanol (or ethyl glycol).
  • the alcohol may contain, for example, 1 to 10 carbon atoms, inclusive of all specific values and subranges therebetween, and 0, 1, 2, 3 (or more) oxygen atoms in addition to the oxygen atom of the hydroxyl group.
  • the alcohol III is expediently used in a considerable stoichiometric excess, preferably a 1- to 10-fold stoichiometric excess, in relation to the halosilane so that it is able to dissolve the hydrogen halide being released.
  • This stoichiometric excess of the alcohol includes all specific values and subranges therebetween, such as 2-, 5-, 6-, 7-, 8- and 9-fold stoichiometric excess.
  • the nonpolar solvent for the halosilanes II and, after the reaction, the alkoxysilanes I must not be miscible with the (polar) alcohol III.
  • the nonpolar solvent is chosen in such a manner that the alcohol III is not dissolved by more than 10%, advantageously not by more than 5%, at 20° C., and, conversely, the alcohol III dissolves the nonpolar solvent only to a corresponding extent.
  • the dielectric constant of the solvent is generally >10.
  • Suitable solvents are, for example, liquid aliphatic or cycloaliphatic hydrocarbons having 5 to 16 carbon atoms, such as pentane, hexane, octane, dodecane and isomers of these hydrocarbons and mixtures of these hydrocarbons and/or their isomers; and aromatic hydrocarbons having 6 to 8 carbon atoms, such as benzene, toluene, the isomeric xylenes and halogenated aliphatic hydrocarbons having 1 to 8 carbon atoms, such as dichloromethane, chloroform and carbon tetrachloride.
  • the nonpolar solvent is expediently used in such an amount that the content of the halosilanes and/or alkoxysilanes dissolved therein is 5 to 30, preferably 10 to 20, percent by weight. These weight percent ranges include all specific values and subranges therebetween. such as 8, 12, 15 and 25% by weight.
  • the reaction according to the invention proceeds, as mentioned, at low temperatures. Expediently, -20 to +60° C., in particular 10 to 30° C., is employed. These temperature ranges include all specific values and subranges therebetween, such as -10, 0, 5, 15 20, 25, 40 and 50° C.
  • the yield of the alkoxysilane may be at least 25%, at least 50%, at least 75%, at least 85%, at least 90%, at least 95%, at least 97% and at least 99%, up to 100%, based on the halosilane, inclusive of all specific values and subranges there between.
  • FIG. 1 is a block diagram of a plant for carrying out the process according to the invention batchwise.
  • the halosilane 20 is charged, together with the solvent 21 and, from the vessel 11, the alcohol 22, into the mixing vessel 12, e.g. a stirred tank, in which the two liquid phases are mixed with one another.
  • the temperature increases in the course of this to 20 to 60° C., depending on the amounts of substances used.
  • the temperature can be controlled by feeding the halosilane 20 and the alcohol 22 into the stirred tank 12 gradually.
  • the stirred tank can have a jacket for the passage of a heat exchange liquid or an attached reflux condenser, so that the boiling point of the solvent determines the reaction temperature.
  • the reaction is generally terminated after 10 minutes to 100 minutes, and the reaction mixture is transferred to the separation vessel 13, in which the lighter nonpolar product phase 23 and the heavier alcohol phase 24 separate.
  • the latter is introduced into the column K3 and is there separated into hydrogen halide 28 and a bottom fraction which is itself fractionated in the column K4 into a top fraction 31, which comprises the alcohol and silanes and can be introduced into a new batch, and a bottom fraction 30 which comprises high-boilers (siloxanes) and can be discarded, for example combusted.
  • the nonpolar product phase 23 is distilled in the column K1.
  • This produces the top product 32 which comprises the reaction product alkoxysilane together with the solvent and small amounts of alcohol and can be separated in a further distillation.
  • the bottom fraction 27 again comprises highboilers (siloxanes) and can be treated in a similar manner to the bottom fraction 30.
  • FIG. 2 is the block diagram of a plant for carrying out the process according to the invention continuously.
  • the chlorosilane 20, dissolved in the nonpolar solvent 21 is continuously introduced as lighter phase into the bottom part of the reaction-extraction column 40.
  • the alcohol 22 is continuously applied as denser phase to the top of the reaction-extraction column 40, in which it moves downwards as a continuous phase in countercurrent to the ascending lighter nonpolar phase which is dispersed in the denser phase.
  • a homogeneous dispersion can be achieved by means of suitable internals or packings of the reaction-extraction column 40 or, particularly advantageously, by pulsation.
  • the nonpolar lighter phase 23 is taken off as overhead product and the denser polar alcohol phase as bottom product 24.
  • Both the nonpolar phase 23 and the polar alcohol phase 24 are continuously worked up in columns.
  • the nonpolar solvent is firstly distilled off together with small amounts of alcohol in the column K1 and can be recycled as stream 25 to the vessel 10.
  • the bottom product of column K1 is passed into column K2, from which the product 26, that is the (completely) alkoxylated alkoxysilane, is taken off as overhead product and the high-boilers 27 are taken off as bottom product.
  • the polar phase 24 is first freed from hydrogen halide 28 in the column K3, and in the column K4, alcohol 22 is removed as overhead product, which can be recycled to the vessel 11.
  • the bottom product of the column K4 is passed into the column K5 in which partially alkoxylated chlorosilane 29 is taken off as overhead product and can be recycled to the vessel 10, while high-boilers 30 are passed into the column K2, in which they are ejected from the process, after removing distillable portions, as a part of the high-boilers 27.
  • monohalosilanes are used as starting materials, no partially alkoxylated silanes are formed.
  • the column K5 can then be omitted and the bottom product of the column K4 is introduced directly into the column K2.
  • CPMDCS (3-chloropropyl)methyldichlorosilane
  • cyclohexane 600 g of a solution of 60 g of (3-chloropropyl)methyldichlorosilane (CPMDCS) in 540 g of cyclohexane are placed into a stirred tank. 110 g of methanol are then added, and the two phases are intensively mixed with one another. The reaction is performed at room temperature for 30 minutes. The two phases are then separated by settling.
  • the denser methanol phase comprises the majority of the hydrogen chloride formed and smaller amounts of CPMDMO and the only mono-alkoxylated (3-chloropropyl)methylchloromethoxysilane (CPMCMO).
  • the tighter cyclohexane phase comprises the majority of the product CPMDMO formed, while the monoalkoxylated CPMCMO is not present in the cyclohexane phase.
  • Table 1 below gives the composition of the two phases as determined by gas chromatography.
  • Methanol is fed in at the top of a continuously operated reaction-extraction column and CPMDCS in cyclohexane is fed in at the bottom.
  • the nonpolar phase is the continuous phase; the alcohol is dispersed in the nonpolar phase at the top of the column using a ring distributor.
  • the CPMDMO-laden cyclohexane phase is taken off at the top of the reaction-extraction column, and the hydrogen chloride-laden alcohol phase is taken off at the bottom of the reaction-extraction column. Both phases are analyzed by means of gas chromatography, Table 2 below shows the streams in g/h, differentiated into feed and output streams and into polar and nonpolar phases
  • CPMDMO The yield of CPMDMO in the two phases is 96%, based on CPMDCS used (and at the same time reacted).
  • CPMCMO Yield 1.7%) is only present in the alcohol phase, and siloxane (yield 2.3%) only in the cyclohexane phase.

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US09/210,735 1997-12-15 1998-12-15 Process for preparing alkoxysilanes Expired - Lifetime US6150550A (en)

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DE19755597A DE19755597A1 (de) 1997-12-15 1997-12-15 Verfahren zur Herstellung von Alkoxysilanen
DE19755597 1997-12-15

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20030030476A (ko) * 2001-10-11 2003-04-18 주식회사 금강고려화학 3-클로로프로필알콕시실란의 제조방법
US20040124144A1 (en) * 2002-10-29 2004-07-01 Antoine Paris Process for the purification of N-carboxyanhydrides of amino acids
US20060167297A1 (en) * 2005-01-27 2006-07-27 Wacker-Chemie Gmbh Continuous process for preparing SiOC-containing compounds
US9340560B2 (en) 2013-02-13 2016-05-17 Evonik Degussa Gmbh Process for esterifying silicon-halogen compounds in a column and apparatus suitable therefor

Families Citing this family (4)

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DE102004025766A1 (de) 2004-05-26 2005-12-22 Degussa Ag Herstellung von Organosilanestern
US7262314B2 (en) * 2004-07-07 2007-08-28 Xerox Corporation 3-iodopropylmethyldiisopropoxysilane and imaging members including the same
DE102006019016A1 (de) * 2006-04-19 2007-10-25 Technische Universität Bergakademie Freiberg Verfahren zur Herstellung von Di- und Trialkoxysilanen
CN101759714B (zh) * 2009-12-31 2013-03-13 蓝星化工新材料股份有限公司江西星火有机硅厂 γ-氯丙基甲基二甲氧基硅烷的制备工艺

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GB674137A (en) * 1949-09-17 1952-06-18 Monsanto Chemicals Improvements relating to ethyl silicate and to its use in the production of refractory materials
DE862895C (de) * 1950-08-23 1953-01-15 Goldschmidt Ag Th Verfahren zur Entfernung des Halogenwasserstoffs aus den Umsetzungsprodukten halogenhaltiger Siliciumverbindungen
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DE3801618A1 (de) * 1988-01-21 1989-07-27 Gewerk Eisenhuette Westfalia Kratzer, insbesondere fuer kettenkratzfoerderer mit doppelmittelkettenband
US5493044A (en) * 1994-10-20 1996-02-20 Fmc Corporation Process for preparing alkylsilyl or arylsilyl ethers

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DE31751C (de) * A. löwengard in Hamburg Schirmgestell, welches die Verwandlung eines Regenschirms in einen Sonnenschirm gestattet
GB674137A (en) * 1949-09-17 1952-06-18 Monsanto Chemicals Improvements relating to ethyl silicate and to its use in the production of refractory materials
DE862895C (de) * 1950-08-23 1953-01-15 Goldschmidt Ag Th Verfahren zur Entfernung des Halogenwasserstoffs aus den Umsetzungsprodukten halogenhaltiger Siliciumverbindungen
DE913769C (de) * 1951-06-06 1954-06-21 Basf Ag Verfahren zur Herstellung von Orthokieselsaeureestern
US3008975A (en) * 1958-06-24 1961-11-14 Union Carbide Corp Process for preparing silicon esters from halosilanes
DE2033373A1 (en) * 1969-07-25 1971-04-01 VEB Chemiekombinat Bitterfeld, χ 4400 Bitterfeld Alkoxy silane prepn
DE2061189A1 (de) * 1970-12-11 1972-06-15 Wacker Chemie Gmbh Verfahren zur kontinuierlichen Herstellung von Alkoxysilanen bzw.Alkoxypolysiloxanen
DE2403731A1 (de) * 1973-01-27 1974-08-01 Scragg & Sons Heizvorrichtung zur thermofixierung der kraeuselung bei thermoplastischen kunststofffaeden oder -fadenbuendeln
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DE2744726A1 (de) * 1977-10-05 1979-04-12 Dynamit Nobel Ag Verfahren zur herstellung von monomeren und oligomeren kieselsaeurealkylestern
DE2800017A1 (de) * 1978-01-02 1979-07-05 Dynamit Nobel Ag Verfahren zur herstellung von organoalkoxysilanen
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DE3236628A1 (de) * 1982-10-04 1984-04-05 Dynamit Nobel Ag, 5210 Troisdorf Verfahren zur kontinuierlichen herstellung von alkoxysilanen
US4642363A (en) * 1984-08-30 1987-02-10 Dynamit Nobel Ag Method of preparing trialkyl organo-oxysilanes
US4851558A (en) * 1987-06-12 1989-07-25 Toshiba Silicone Co., Ltd. Process for producing alkoxysilanes
DE3801618A1 (de) * 1988-01-21 1989-07-27 Gewerk Eisenhuette Westfalia Kratzer, insbesondere fuer kettenkratzfoerderer mit doppelmittelkettenband
US5493044A (en) * 1994-10-20 1996-02-20 Fmc Corporation Process for preparing alkylsilyl or arylsilyl ethers

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20030030476A (ko) * 2001-10-11 2003-04-18 주식회사 금강고려화학 3-클로로프로필알콕시실란의 제조방법
US20040124144A1 (en) * 2002-10-29 2004-07-01 Antoine Paris Process for the purification of N-carboxyanhydrides of amino acids
US20060167297A1 (en) * 2005-01-27 2006-07-27 Wacker-Chemie Gmbh Continuous process for preparing SiOC-containing compounds
KR100740290B1 (ko) 2005-01-27 2007-07-18 와커 헤미 아게 ＳｉＯＣ 함유 화합물의 연속식 제조 방법
US7339069B2 (en) 2005-01-27 2008-03-04 Wacker Chemie Ag Continuous process for preparing SiOC-containing compounds
CN100436509C (zh) * 2005-01-27 2008-11-26 瓦克化学股份公司 用于制造含SiOC的化合物的连续方法
US9340560B2 (en) 2013-02-13 2016-05-17 Evonik Degussa Gmbh Process for esterifying silicon-halogen compounds in a column and apparatus suitable therefor

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EP0924215B1 (de) 2003-02-05
JP4263288B2 (ja) 2009-05-13
EP0924215A2 (de) 1999-06-23
DE19755597A1 (de) 1999-06-17
DE59807115D1 (de) 2003-03-13
EP0924215A3 (de) 1999-10-06
JPH11236390A (ja) 1999-08-31

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